Helical nanostructures self-assembled from optically active phthalocyanine derivatives bearing four optically active binaphthyl moieties: Effect of metal-ligand coordination on the morphology, dimension, and helical pitch of self-assembled nanostructures

Langmuir

Volumn 26, Issue 10, 2010, Pages 7489-7497

  Wu, Lizhen ^a   Wang, Quanbo ^a   Lu, Jitao ^a   Bian, Yongzhong ^b   Jiang, Jianzhuang ^a,b   Zhang, Xiaomei ^a  

^a SHANDONG UNIVERSITY   (China)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY BEIJING   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BINAPHTHYL; BINAPHTHYL MOIETY; BIPYRIDINES; CHIRAL DISCRIMINATION; CIRCULAR DICHROISM; COORDINATION BONDS; ELECTRONIC ABSORPTION; HELICAL NANOSTRUCTURES; HELICAL PITCH; HELICITIES; LIGAND COORDINATION; METAL-FREE PHTHALOCYANINE; NITROGEN ATOM; OPTICALLY ACTIVE; ORGANIC BASE; PHTHALOCYANINE DERIVATIVES; PHTHALONITRILES; SELF ASSEMBLED NANOSTRUCTURES; SELF-ASSEMBLED; SEM; SIDE CHAINS; TEM; TETRAKIS; TETRAMERIZATION; ZINC COMPLEX;

CHIRALITY; CIRCULAR DICHROISM SPECTROSCOPY; COMPLEXATION; DICHROISM; ENANTIOMERS; LIGANDS; METALS; MOLECULES; MORPHOLOGY; NANOSTRUCTURES; NITROGEN COMPOUNDS; SELF ASSEMBLY; STEREOCHEMISTRY; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS; X RAY PHOTOELECTRON SPECTROSCOPY; ZINC;

SCANNING ELECTRON MICROSCOPY;

INDOLE DERIVATIVE; LIGAND; NANOMATERIAL; NAPHTHALENE DERIVATIVE; ORGANOMETALLIC COMPOUND; PHTHALOCYANINE; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PARTICLE SIZE; STEREOISOMERISM; SURFACE PROPERTY;

INDOLES; LIGANDS; MOLECULAR STRUCTURE; NANOSTRUCTURES; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; PARTICLE SIZE; STEREOISOMERISM; SURFACE PROPERTIES; ZINC;

EID: 77952413048     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la100061e     Document Type: Article

References (77)

1. Garoff, R. A., Litzinger, E. A., Connor, R. E., Fishman, I., and Armitage, B. A. Langmuir 2002, 18, 6330-6337
2. Wang, M., Silva, G. L., and Armitage, B. A. J. Am. Chem. Soc. 2000, 122, 9977-9986
3. Pasternack, R. F., Giannetto, A., Pagano, P., and Gibbs, E. J. J. Am. Chem. Soc. 1991, 113, 7799-7780
4. Hannah, K. C. and Armitage, B. A. Acc. Chem. Res. 2004, 37, 845-853
5. Chen, X. and Liu, M. J. Inorg. Biochem. 2003, 94, 106-113
6. Schmuck, C. Angew. Chem., Int. Ed. 2003, 42, 2448-2452
7. Nelson, J. C., Saven, J. G., Moore, J. S., and Wolynes, P. G. Science 1997, 277, 1793-1796
8. Cornelissen, J. J. L. M., Fisher, M., Sommerdijk, N. A. J. M., and Nolte, R. J. M. Science 1998, 280, 1427-1430
9. Oda, R., Schmutz, M., Candau, S. J., and MacKintosh, F. C. Nature 1999, 399, 566-569
10. Hirschberg, J. H. K. K., Brunsveld, L., Ramzi, A., Vekemans, J. A. J. M., Sijbesma, R. P., and Meijer, E. W. Nature 2000, 407, 167-170
11. Berl, V., Huc, I., Khoury, R. G., Krische, M. J., and Lehn, J.-M. Nature 2000, 407, 720-723
12. Zubarev, E. R., Pralle, M. U., Sone, E. D., and Stupp, S. I. J. Am. Chem. Soc. 2001, 123, 4105-4106
13. Sone, E. D., Zubarev, E. R., and Stupp, S. I. Angew. Chem., Int. Ed. 2002, 41, 1706-1709
14. Fenniri, H., Deng, B.-L., and Ribbe, A. E. J. Am. Chem. Soc. 2002, 124, 11064-11072
15. Giorgi, T., Lena, S., Mariani, P., Cremonini, M. A., Masiero, S., Pieraccini, S., Rabe, J. P., Samori, P., Spada, G. P., and Gottarelli, G. J. Am. Chem. Soc. 2003, 125, 14741-14749
16. Xiao, J., Xu, J., Cui, S., Liu, H., Wang, S., and Li, Y. Org. Lett. 2008, 10, 645-648
17. Ishi-I, T., Kuwahara, R., Takata, A., Jeong, Y., Sakurai, K., and Mataka, S. Chem. - Eur. J. 2006, 12, 763-776
18. Roman, A. E. and Nolte, R. J. M. Angew. Chem., Int. Ed. 1998, 37, 63-68
19. Yashima, E., Maeda, K., and Okamoto, Y. Nature 1999, 399, 449-451
20. Pantos, G. D., Wietor, J. L., and Sanders, J. K. M. Angew. Chem., Int. Ed. 2007, 46, 2238-2240
21. Cornelissen, J. J. L. M., Rowan, A. E., Nolte, R. J. M., and Sommerdijk, N. A. J. M. Chem. Rev. 2001, 101, 4039-4070
22. Palmans, A. R. A., Vekemans, J. A. J. M., Havinga, E. E., and Meijer, E. W. Angew. Chem., Int. Ed. 1997, 36, 2648-2651
23. Stupp, S. I., LeBonheur, V., Walker, K., Li, L. S., Huggins, K. E., Keser, M., and Amstutz, A. Science 1997, 276, 384-389
24. Prins, L. J., Huskens, J., F. Jong, D., and Timmerman, P. Nature 1999, 398, 498-502
25. Lever, A. B. P. and Leznoff, C. C. Phthalocyanine: Properties and Applications; VCH: New York, 1989-1996; Vols. 1-4.
26. McKeown, N. B. Phthalocyanines Materials: Synthesis, Structure and Function; Cambridge University Press: New York, 1998.
27. Kadish, K. M., Smith, K. M., and Guilard, R. The Porphyrin Handbook; Academic Press: San Diego, 2000-2003; Vols. 1-20.
28. Kimura, M., Narikawa, H., Ohta, K., and Hanabusa, K. Chem. Mater. 2002, 14, 2711-2717
29. Huang, X., Zhao, F., Li, Z., Tang, Y., Zhang, F., and Tung, C. Langmuir 2007, 23, 5167-5172
30. de la Escosura, A., Díaz, M. V. M., Thordarson, P., Rowan, A. E., Nolte, R. J. M., and Torres, T. J. Am. Chem. Soc. 2003, 125, 12300-12308
31. Chen, P., Ma, X., and Liu, M. Macromolecules 2007, 40, 4780-4784
32. Kobayashi, N. Coord. Chem. Rev. 2001, 219-221, 99-123
33. Liu, H., Liu, Y., Liu, M., Chen, C., and Xi, F. Tetrahedron Lett. 2001, 42, 7083-7086
34. Liu, H., Chen, C., Ai, M., Gong, A., Jiang, J., and Xi, F. Tetrahedron Asymmetry 2000, 11, 4915-4922
35. Kobayashi, N. Chem. Commun. 1998, 487-488
36. Kobayashi, N., Kobayashi, Y., and Osa, T. J. Am. Chem. Soc. 1993, 115, 10994-10995
37. Kimura, M., Ueki, H., Ohta, K., Shirai, H., and Kobayashi, N. Langmuir 2006, 22, 5051-5056
38. Kimura, M., Kuroda, T., Ohta, K., Hanabusa, K., Shirai, H., and Kobayashi, N. Langmuir 2003, 19, 4825-4830
39. Engelkamp, H., Middelbeek, S., and Nolte, R. J. M. Science 1999, 284, 785-788
40. Lv, W., Wu, X.; Wu, Bian, Y., Jiang, J., and Zhang, X. ChemPhysChem 2009, 10, 2725-2732
41. Rai, R., Saxena, A., Ohira, A., and Fujiki, M. Langmuir 2005, 21, 3957-3962
42. John, G., Jung, J. H., Minamikawa, H., Yoshida, K., and Shimizu, T. Chem. - Eur. J. 2002, 8, 493-497
43. Thomas, B. N., Lindemann, C. M., Corcoran, R. C., Cotant, C. L., Kirshch, J. E., and Persichini, P. J. J. Am. Chem. Soc. 2002, 124, 1227-1233
44. Svenson, S. and Messersmith, P. B. Langmuir 1999, 15, 4464-4471
45. Adachi, K., Chayama, K., and Watarai, H. Langmuir 2006, 22, 1630-1639
46. Adachi, K., Chayama, K., and Watarai, H. Chirality 2006, 18, 599-608
47. Balakrishnan, K., Datar, A., Oitker, R., Chen, H., Zuo, J., and Zang, L. J. Am. Chem. Soc. 2005, 127, 10496-10497
48. Su, W., Zhang, Y., Zhao, C., Li, X., and Jiang, J. ChemPhysChem 2007, 8, 1857-1862
49. Lu, G., Zhang, X., Cai, X., and Jiang, J. J. Mater. Chem. 2009, 2417-2424
50. Gong, X., Milic, T., Xu, C., Batteas, J. D., and Drain, C. M. J. Am. Chem. Soc. 2002, 124, 14290-14291
51. Lu, G., Chen, Y., Zhang, Y., Bao, M., Bian, Y., Li, X., and Jiang, J. J. Am. Chem. Soc. 2008, 130, 11623-11630
52. Gao, Y., Zhang, X., Ma, C., Li, X., and Jiang, J. J. Am. Chem. Soc. 2008, 130, 17044-17052
53. Li, R., Zhang, X., Zhu, P., Ng, D. K. P., Kobayashi, N., and Jiang, J. Inorg. Chem. 2006, 45, 2327-2334
54. Bian, Y., Li, L., Dou, J., Cheng, D. Y. Y., Li, R., Ma, C., Ng, D. K. P., Kobayashi, N., and Jiang, J. Inorg. Chem. 2004, 43, 7539-7544
55. Zhang, Y., Zhang, X., Liu, Z., Bian, Y., and Jiang, J. J. Phys. Chem. A 2005, 109, 6363-6370
56. Sheng, N., Li, R., Choi, C.-F., Su, W., Ng, D. K. P., Cui, X., Yoshida, K., Kobayashi, N., and Jiang, J. Inorg. Chem. 2006, 45, 3794-3802
57. In order to clearly compare the electronic absorption and circular dichroism spectra of the (R)- and (S)-ZnPc (2) in dilute chloroform with their aggregates fabricated from (R)- and (S)- 2 with and without the addition of 4,4′-bipyridine, the electronic absorption and circular dichroism spectra of (R)- and (S)- 2 in dilute chloroform are shown in Figure 2 B, E, A, and D.
58. Harada, H. and Nakanishi, K. Circular Dichroic Spectroscopy, Exciton Coupling in Organic Stereochemistry University Science Books: New York, 1983.
59. Kobayashi, N. Chem. Commun. 1998, 487-488
60. Kasha, M., Rawls, H. R., and EI-Bayoumi, M. A. Pure Appl. Chem. 1965, 11, 371-392
61. Gao, Y., Chen, Y., Li, R., Bian, Y., Li, X., and Jiang, J. Chem. - Eur. J. 2009, 15, 13241-13252
62. Berova, N., Nakanishi, K., and Woody, R. CircularDichroism: Princples and Applications, 2 nd ed.; Wiley-VCH: New York, 2000; pp 337 - 382.
63. Hofacker, A. L. and Parquette, J. R. Angew. Chem., Int. Ed. 2005, 44, 1053-1057
64. Balaz, M., Holmes, A. E., Benedetti, M., Rodriguez, P. C., Berova, N., Nakanishi, K., and Proni, G. J. Am. Chem. Soc. 2005, 127, 4172-4173
65. Borovkov, V. V., Lintuluoto, J. M., Fujiki, M., and Inoue, Y. J. Am. Chem. Soc. 2000, 122, 4403-4407
66. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Pople, J. A. Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
67. Janczak, J. and Idemori, Y. M. Inorg. Chem. 2002, 41, 5059-5065
68. Gardberg, A. S., Yang, S., Hoffman, B. M., and Ibers, J. A. Inorg. Chem. 2002, 41, 1778-1781
69. Soldatov, D. V., Tinnemans, P., Enright, G. D., Ratcliffe, C. I., Diamente, P. R., and Ripmeester, J. A. Chem. Mater. 2003, 15, 3826-3840
70. Litvinov, A. L., Konarev, D. V., Kovalevsky, A. Yu., Neretin, I. S., Coppens, P., and Lyubovskaya, R. N. Cryst. Growth Des. 2005, 5, 1807-1819
71. Shukla, A. D., Dave, P. C., Suresh, E., Das, A., and Dastidar, P. J. Chem. Soc., Dalton Trans. 2000, 4459-4463
72. Haas, M., Liu, S.-X., Neels, A., and Decurtins, S. Eur. J. Org. Chem. 2006, 5467-5478
73. Zeng, Q., Wu, D., Wang, C., Lu, J., Ma, B., Shu, C., Ma, H., Li, Y., and Bai, C. CrystEngComm 2005, 7, 243-248
74. Geiss, A. and Vahrenkamp, H. Inorg. Chem. 2000, 39, 4029-4036
75. Hunsicker, R. A. and Klier, K. Chem. Mater. 2002, 14, 4807-4811
76. Gaskell, K. J., Starace, A., and Langell, M. A. J. Phys. Chem. C 2007, 111, 13912-13921
77. Mielczarski, J. A., Cases, J. M., Alnot, M., and Ehrhardt, J. J. Langmuir 1996, 12, 2531-2543